SEC542: Web App Penetration Testing and Ethical Hacking

With the infinite tools used for web application penetration, SEC542 helps you understand and use the best tools for your environment.

Linh Sithihao, UT South Western Medical Center

Great course. Good content. As mentioned in class, the web app penetration testing space is huge. SEC542 was a solid way to begin my adventure into the space.

Joel Fyan, HP

Web applications play a vital role in every modern organization. But, if your organization does not properly test and secure its web apps, adversaries can compromise these applications, damage business functionality, and steal data. Unfortunately, many organizations operate under the mistaken impression that a web application security scanner will reliably discover flaws in their systems.

Customers expect web applications to provide significant functionality and data access. Even beyond the importance of customer-facing web applications, internal web applications increasingly represent the most commonly used business tools within any organization. Unfortunately, there is no "patch Tuesday" for custom web applications, so major industry studies find that web application flaws play a major role in significant breaches and intrusions. Adversaries increasingly focus on these high-value targets either by directly abusing public-facing applications or by focusing on web apps as targets after an initial break-in.

SEC542 enables students to assess a web application's security posture and convincingly demonstrate the impact of inadequate security that plagues most organizations.

Students will come to understand major web application flaws and their exploitation and, most importantly, learn a field-tested and repeatable process to consistently find these flaws and convey what they have learned to their organizations. Even technically gifted security geeks often struggle with helping organizations understand risk in terms relatable to business. Much of the art of penetration testing has less to do with learning how adversaries are breaking in than it does with convincing an organization to take the risk seriously and employ appropriate countermeasures. The goal of SEC542 is to better secure organizations through penetration testing, and not just show off hacking skills. The course will help you demonstrate the true impact of web application flaws through exploitation.

In addition to high-quality course content, SEC542 focuses heavily on in-depth, hands-on labs to ensure that students can immediately apply all they learn.

In addition to more than 30 formal hands-on labs, the course culminates in a web application pen test tournament, powered by the SANS NetWars Cyber Range. This Capture the Flag event on the final day brings students into teams to apply their newly acquired command of web application penetration testing techniques in a fun way to hammer home lessons learned.

Course Syllabus

SEC542.1: Introduction and Information Gathering

Overview

Understanding the attacker's perspective is key to successful web application penetration testing. The course begins by thoroughly examining web technology, including protocols, languages, clients, and server architectures, from the attacker's perspective. We also examine different authentication systems, including Basic, Digest, Forms, and Windows Integrated authentication, and discuss how servers use them and attackers abuse them. After authentication, we analyze the importance of encryption and HTTPS. Before leaving HTTPS, we dive into the infamous Heartbleed flaw and get our first taste of exploitation with a hands-on lab.

We then turn to the four steps that make up our process for conducting web application penetration tests: reconnaissance, mapping, discovery, and exploitation. On the first day, we review the fundamental principles of each phase and discuss how penetration testers can use them together as a cyclical in-depth attack process. We then cover the types of penetration testing and what pieces need to be part of a thorough, high-value pen test report. To complete the course day, we explore aspects of a vulnerable web application using Burp Suite.

CPE/CMU Credits: 6

Topics

Overview of the web from a penetration tester's perspective

Exploring the various servers and clients

Discussion of the various web architectures

Discovering how session state works

Discussion of the different types of vulnerabilities

WHOIS and DNS reconnaissance

The HTTP protocol

WebSocket

Secure Sockets Layer (SSL) configurations and weaknesses

Heartbleed exploitation

Utilizing the Burp Suite in web app penetration testing

SEC542.2: Configuration, Identity, and Authentication Testing

Overview

The second day begins with the reconnaissance and mapping phases of a web app penetration test. Reconnaissance includes gathering publicly available information regarding the target application and organization, identifying the machines that support our target application, and building a profile of each server, including the operating system, specific software, and configuration. The discussion is underscored through several practical, hands-on labs in which we conduct reconnaissance against in-class targets.

In the mapping phase, we build a map or diagram of the application's pages and features. This phase involves identifying the components, analyzing the relationship between them, and determining how the pieces work together. We often discover configuration flaws in web application infrastructure components during the mapping phase. After discussion of these types of flaws, we use the Shellshock vulnerability as an opportunity to get deeper hands-on experience with Burp Suite, cURL, and manual exploitation techniques. We then dive deep into spidering/crawling web applications. Spidering represents a vital part of both the mapping phase and the overall penetration test.

CPE/CMU Credits: 6

Topics

Scanning with Nmap

Discovering the infrastructure within the application

Identifying the machines and operating systems

Exploring virtual hosting and its impact on testing

Learning methods to identify load balancers

Software configuration discovery

Learning tools to spider a website

Brute forcing unlinked files and directories

Discovering and exploiting Shellshock

Web authentication

Username harvesting and password guessing

Fuzzing

Burp Intruder

SEC542.3: Injection

Overview

This section continues to explore our methodology with the discovery phase. We build on the information identified during the mapping phase, exploring methods to find and verify vulnerabilities within the application. Students also begin to explore the interactions between the various vulnerabilities.

This course day dives deeply into vital manual testing techniques for vulnerability discovery. To facilitate manual testing, we kick off the day with an introduction to Python and a hands-on lab working with it.

In addition to custom scripts, we focus on developing in-depth knowledge of interception proxies for web application vulnerability discovery. A highlight of the day involves spending significant time working with both traditional and blind SQL injection flaws.

Throughout the discovery phase, we will explore both manual and automated methods of discovering vulnerabilities within applications and discuss the circumstances under which each is appropriate.

CPE/CMU Credits: 6

Topics

Session tracking

Authentication bypass flaws

Mutillidae

Command Injection

Directory traversal

Local File Inclusion (LFI)

Remote File Inclusion (RFI)

SQL injection

Blind SQL injection

Error-based SQL injection

Exploiting SQL injection

SQL injection tools

sqlmap

SEC542.4: XXE and XSS

Overview

On day four, students continue exploring the discovery phase of the methodology. We cover methods to discover key vulnerabilities within web applications, such as Cross-Site Scripting (XSS) and Cross-Site Request Forgery (CSRF/XSRF). Manual discovery methods are employed during hands-on labs.

The course day will also include a detailed discussion of AJAX as we explore how it enlarges the attack surface leveraged by penetration testers. We also analyze how AJAX is affected by other vulnerabilities already covered in depth earlier in the course.

After detailing the various vulnerabilities and manual discovery methods, day four concludes with a review of various automated web application vulnerability scanners, to complement our previous coverage of manual techniques with scripting, ZAP, and the Burp Suite.

CPE/CMU Credits: 6

Topics

XML External Entity (XXE)

Cross-Site Scripting (XSS)

Browser Exploitation Framework (BeEF)

AJAX

XML and JSON

Document Object Model (DOM)

Logic attacks

API attacks

Data attacks

SEC542.5: CSRF, Logic Flaws and Advanced Tools

Overview

On the fifth day, we launch actual exploits against real-world applications, building on the previous three steps, expanding our foothold within the application, and extending it to the network on which it resides. As penetration testers, we specifically focus on ways to leverage previously discovered vulnerabilities to gain further access, highlighting the cyclical nature of the four-step attack methodology.

During our exploitation phase, we expand our use of tools such as ZAP and the Burp Suite, and complement them with further use of sqlmap, BeEF, the Browser Exploitation Framework, and Metasploit to help craft exploits against various web applications. We launch SQL injection, Cross-Site Scripting (XSS), and Cross-Site Request Forgery attacks, amongst others. In class we exploit these flaws to perform data theft, hijack sessions, steal passwords, get shells, pivot against connected networks, and much more. Through various forms of exploitation, the student gains a keen understanding of the potential business impact of these flaws to an organization.

CPE/CMU Credits: 6

Topics

Cross-Site Request Forgery (CSRF)

Python for web app penetration testing

WPScan

w3af

Metasploit for web penetration testers

Leveraging attacks to gain access to the system

How to pivot our attacks through a web application

Exploiting applications to steal cookies

Executing commands through web application vulnerabilities

When tools fail

SEC542.6: Capture the Flag

Overview

On day six, students form teams and compete in a web application penetration testing tournament. This NetWars-powered Capture the Flag exercise provides students an opportunity to wield their newly developed or further honed skills to answer questions, complete missions, and exfiltrate data, applying skills gained throughout the course. The style of challenge and integrated hint system allows students of various skill levels to both enjoy a game environment and solidify the skills learned in class.

CPE/CMU Credits: 6

Additional Information

Laptop Required

Security 542 requires a Windows, Linux or Macintosh computer with the following minimum hardware requirements:

CPU: 2.0+ processor

RAM: 4 GB or higher

20 GB free hard disk space

USB port

Ethernet adapter (A wired connection is required in class. If your laptop supports only wireless, please make sure to bring an Ethernet adapter with you.)

Please install the following software on the computer:

VMware Workstation 9, Player 5, or Fusion 5 (or newer)

You must have the ability to disable the host firewall (Windows firewall or other third-party firewall), antivirus programs, or other security software running on your desktop. This usually means you need to have administrative privileges on the machine.

DO NOT plan on just killing your antivirus service or processes, because most antivirus tools still function even when their associated services and processes have been terminated.

If you have additional questions about the laptop specifications, please contact laptop_prep@sans.org.

Who Should Attend

General security practitioners

Penetration testers

Ethical hackers

Web application developers

Website designers and architects

Justify Your Training

Use this sample training request letter, or elements of it, to justify the time and budget required to complete SANS training to your manager. Simply copy and paste text into an email to your manager, then make any necessary adjustments to personalize the information.

Prerequisites

SEC542 assumes students have a basic working knowledge of the Linux command line.

Use the Browser Exploitation Framework (BeEF) to hook victim browsers, attack client software and the network, and evaluate the potential impact that XSS flaws have within an application.

Perform a complete web penetration test during the Capture the Flag exercise to bring techniques and tools together into a comprehensive test.

Hands-on Training

SANS SEC542 employs hands-on labs throughout the course to further students' understanding of web application penetration concepts. Some of the many hands-on labs in the course include:

Assessing Web Authentication

Heartbleed Exploitation

Mobile Application MITM

Reflective XSS Attacks

Persistent XSS Attacks

SQL Injection

Blind SQL Injection

CSRF Exploitation

Metasploit for Web Application Attacks

Exploiting Shellshock

Leveraging the sqlmap tool

BeEF and Browser Exploitation

Session Hijacking

Username Harvesting

HTML Injection

Remote File Inclusion

Local File Inclusion

OS Command Injection

Drupalgeddon Exploitation

w3af

Python for Web Application Pen Testers

Pen Testing with JavaScript

Extensive use of both Burp Suite and ZAP throughout the course

Press & Reviews

"This course taught me to truly focus on the methodology while performing a pen test. During the Capture the Flag event, I realized how much time can be wasted if you fail to respect your methodology." - Sean Rosado, RavenEye

"The SEC542 tools and course presentation are top-notch. I will be using this material extensively." - Jeremy Pierson, Academy Mortgage

"With the infinite tools used for web application penetration, SEC542 helps you understand/use the best tools for your environment." - Linh Sithihao, UT South Western Medical Center

"Every class gives you invaluable information from real-world testing you cannot find in a book." - David Fava, The Boeing Company

Author Statement

Students routinely show up to SEC542 having been demoralized by their organization's web application vulnerability scanner. Sitting on the business end of these scanners, students regularly attest to 1,000+ pages of output littered with false positives. One of the most rewarding aspects of teaching SEC542 is seeing and hearing those very same students' enthusiasm for applying the skills they have learned through the week to the applications they are responsible for securing. They intrinsically knew the push-button approach to penetration testing was failing them, but lacked the knowledge and skill to ably and efficiently perform any other style of assessment. We are happy to say that SEC542 remedies this problem. Students walk away from class with a deep knowledge of key web application flaws and how to discover and exploit them, as well as how to present these findings in an impactful way. - Seth Misenar and Eric Conrad

Additional Resources

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